Leonard can test free agency in the summer of 2019, so Raptors president of basketball operations Masai Ujiri took significant risk with the transaction. Ujiri made the deal with a determination that he can convince Leonard to re-sign with the Raptors next summer in free agency, sources told ESPN's Adrian Wojnarowski.

The Raptors would be able to offer Leonard a five-year, $190 million contract next summer. If Leonard leaves the Raptors, he could sign a four-year, $141 million deal with a team with the available salary-cap space.

So far, Leonard's preference is to sign in Los Angeles with either the Lakers or Clippers next season, sources told Wojnarowski.